Constituents from the Leaves of Phellodendron amurense var. wilsonii and Their Bioactivity

Abstract

Two new dihydroflavonols, phellodensin-A (1) and phellodensin-C (2); three new coumarins, phellodenol-A (3), phellodenol-B (4), and phellodenol-C (5); one new chlorophyll, phellophyll-a (6); and one new phenyllactate, (2R)-sodium 3-phenyllactate (7), in addition to 35 known compounds have been isolated from the leaves of Phellodendron amurense var. wilsonii. The structures of the new compounds were established based on 1D, 2D NMR and mass spectral analyses. The stereochemistry at the C-2, C-3, and C-2' ' positions of new dihydroflavonol 1 was determined by CD spectroscopy. The known compounds were identified by comparison with authentic samples. The antioxidant and antityrosinase activities were also described.

Constituents from the Leaves of Phellodendron amurense and Their Antioxidant Activity

“…1) and 29 known compounds. The known compounds were identified as amurensin (5), 6) phellamurin (6), 6) kaempferol (7), 10) kaempferol-3-O-b-D-glucoside (8), 10) kaempferol-3-O-b-D-galactoside (9), 11) quercetin (10), 12) quercetin-3-O-b-D-glucoside (11), 10) quercetin-3-Ob-D-galactoside (12), 13) flavaprenin 7,4Ј-diglucoside (13), 14) hexandraside E (14), 15) umbelliferon (15), 16) esculetin (16), 17) phellodenol A (17), 7) scopoletin (18), 16) demethylsuberosin (19), 18) 7-hydroxy-6-(2-hydroxy-3-methyl-3-butenyl) coumarin (20), 19) scoparone (21), 20) xanthyletin (22), 21) skimmin (23), 22) p-hydroxybenzaldehyde (24), 23) methylparaben (25), 24) p-hydroxybenzoic acid (26), 23) anisaldehyde (27), 25) methyl p-anisate (28), 26) sodium (2R) 3-phenyllactate (29), 7) methyl caffeate (30), 6) ferulic acid (31), 27) lupenone (32), 28) and 2-acetyl-5-methoxyfuran (33) 29) by comparison of their spectra with literature data.…”

“…[3][4][5][6][7][8][9] In our ongoing investigation of biologically active compounds form the titled plant, we have isolated three new coumarins and a new glutaric acid derivative along with twenty-nine known compounds from the CHCl 3 soluble portion of the MeOH extract of the leaves of the P. amurense. In this paper, we describe the isolation, structure elucidation of four new compounds and DPPH radical scavenging activity of the compounds.…”

Two New Cytotoxic Phenylallylflavanones from Mexican Propolis

“…The typical absorptions at 293 and 327 nm as well as their corresponding cotton effects ([q] 293 Ϫ7699; [q] 327 ϩ3471) observed in circular dichroism (CD) spectrum indicated a 2R-configuration in 1. 20,21) Since a trans relationship between H-2 and H-3 was assigned on the basis of their coupling constant (J 2,3 ϭ11.4 Hz), 21) the absolute configuration at C-3 was determined to be R. However, the absolute configuration at C-7Љ could not be determined because of the limited amount of available compound isolated. Thus, 1 was identified as (2R,3R)-6-[1-(4Ј-hydroxy-3Ј-methoxyphenyl)prop-2-en- (Fig.…”

Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity

“…In addition, thirty known compounds, amurensin (2), 7) phellamurin (4), 7) quercetin (6), 9) phellodensin-A (7), 10) phellodensin-B (8), 11) rutaecarpine (9), 12) 3-formylindole (10), 13) umbelliferone (11), 14) esculetin (12), 15) scopoletin (13), 14) scoparone (14), 14) columbianetin (15), 16) p-hydroxybenzaldehyde (16), 17) methylparaben (17), 18) p-hydroxybenzoic acid (18), 17) methyl p-anisate (19), 19) vanillic acid (20), 17) methyl p-hydroxycinnamate (21), 17) methyl caffeate (22), 20) benzoic acid (23), 21) p-coumaric acid (24), 22) caffeic acid (25), 23) phellodenin-A (26), 24) lupenone (27), 25) b-sitosterol (28), 26) friedelin (29), 27) 3-epilupeol (30), 28) N-p-coumaroyltyramine (31), 29) N-trans-cinnamoyltyramine (32), 29) and grasshopperketone (33) 30) were also isolated from the leaves of P. japonicum. Among these compounds, all except 2 and 4 were isolated for the first time form P. japonicum.…”